CA2692013C - Modulateurs du recepteur ccr9 et leurs procedes d'utilisation - Google Patents

Modulateurs du recepteur ccr9 et leurs procedes d'utilisation Download PDF

Info

Publication number: CA2692013C
Authority: CA; Canada
Prior art keywords: mmol; thiophene; alkyl; tert; butyl
Prior art date: 2007-07-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA2692013A

Other languages

English (en)

Other versions

CA2692013A1 (fr

Inventor

Eric C. Anderson

Ronald J. Biediger

Jie Chen

Brian Dupre

Pedro Lory

Robert V. Market

Keith A. Monk

Michael M. Savage

Reginald Tennyson

Brandon M. Young

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Encysive Pharmaceuticals Inc

Original Assignee

Encysive Pharmaceuticals Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-07-30

Filing date

2008-07-28

Publication date

2012-08-28

2008-07-28 Application filed by Encysive Pharmaceuticals Inc filed Critical Encysive Pharmaceuticals Inc

2009-02-05 Publication of CA2692013A1 publication Critical patent/CA2692013A1/fr

2012-08-28 Application granted granted Critical

2012-08-28 Publication of CA2692013C publication Critical patent/CA2692013C/fr

Status Expired - Fee Related legal-status Critical Current

2028-07-28 Anticipated expiration legal-status Critical

Links

238000000034 method Methods 0.000 title abstract description 25
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150000001875 compounds Chemical class 0.000 claims abstract description 194
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
201000010099 disease Diseases 0.000 claims abstract description 22
-1 aralkenyl Chemical group 0.000 claims description 158
125000000217 alkyl group Chemical group 0.000 claims description 93
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125000000753 cycloalkyl group Chemical group 0.000 claims description 46
125000001072 heteroaryl group Chemical group 0.000 claims description 44
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125000005843 halogen group Chemical group 0.000 claims description 36
125000000623 heterocyclic group Chemical group 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 36
125000003342 alkenyl group Chemical group 0.000 claims description 29
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
125000000304 alkynyl group Chemical group 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 23
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150000003839 salts Chemical class 0.000 claims description 19
125000001188 haloalkyl group Chemical group 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 16
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125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 8
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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229910052760 oxygen Inorganic materials 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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229910052794 bromium Inorganic materials 0.000 claims description 2
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230000000694 effects Effects 0.000 abstract description 18
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239000012047 saturated solution Substances 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
CRDYSYOERSZTHZ-UHFFFAOYSA-M selenocyanate Chemical compound [Se-]C#N CRDYSYOERSZTHZ-UHFFFAOYSA-M 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
230000008454 sleep-wake cycle Effects 0.000 description 1
208000014964 small bowel Crohn disease Diseases 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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239000001488 sodium phosphate Substances 0.000 description 1
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239000012265 solid product Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
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239000012177 spermaceti Substances 0.000 description 1
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125000005017 substituted alkenyl group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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235000019303 thiodipropionic acid Nutrition 0.000 description 1
230000009974 thixotropic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
125000005591 trimellitate group Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
229920011532 unplasticized polyvinyl chloride Polymers 0.000 description 1
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238000001291 vacuum drying Methods 0.000 description 1
229940120293 vaginal suppository Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
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229920003169 water-soluble polymer Polymers 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D333/40—Thiophene-2-carboxylic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA2692013A 2007-07-30 2008-07-28 Modulateurs du recepteur ccr9 et leurs procedes d'utilisation Expired - Fee Related CA2692013C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US96264007P	2007-07-30	2007-07-30
US60/962,640		2007-07-30
PCT/US2008/009142 WO2009017719A2 (fr)	2007-07-30	2008-07-28	Modulateurs du récepteur ccr9 et leurs procédés d'utilisation

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CA2692013A1 CA2692013A1 (fr)	2009-02-05
CA2692013C true CA2692013C (fr)	2012-08-28

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EP (1)	EP2220065A2 (fr)
KR (1)	KR20100033418A (fr)
AU (1)	AU2008282903B2 (fr)
CA (1)	CA2692013C (fr)
MX (1)	MX2010001187A (fr)
SG (1)	SG183667A1 (fr)
WO (1)	WO2009017719A2 (fr)

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PE20120008A1 (es)	2009-01-12	2012-01-24	Icagen Inc	Derivados de fenoxi bencenosulfonamida
JP2013525368A (ja) *	2010-04-23	2013-06-20	キネタ・インコーポレイテツド	抗ウイルス性化合物
JP5872552B2 (ja)	2010-07-09	2016-03-01	ファイザー・リミテッドＰｆｉｚｅｒＬｉｍｉｔｅｄ	化学化合物
MX339201B (es) *	2010-10-12	2016-05-13	Zafgen Inc	Compuestos de sulfonamida y métodos para elaborarlos y usarlos.
TW201512171A (zh)	2013-04-19	2015-04-01	Pfizer Ltd	化學化合物
JP7847152B2 (ja) *	2021-10-28	2026-04-16	四国化成工業株式会社	チオフェン化合物、その合成方法および該チオフェン化合物を含有する組成物

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JP2001503037A (ja) *	1996-10-16	2001-03-06	アメリカン・サイアナミド・カンパニー	マトリクス金属プロテナイーゼおよびｔａｃｅに対する阻害薬としてのオルト―スルホンアミドヘテロアリールヒドロキサム酸の製造および使用
JP3972163B2 (ja) *	1999-06-18	2007-09-05	株式会社大塚製薬工場	ホスホン酸ジエステル誘導体
US7319111B2 (en) *	2003-02-20	2008-01-15	Encysive Pharmaceuticals, Inc.	Phenylenediamine Urotensin-II receptor antagonists and CCR-9 antagonists

2008
- 2008-07-28 CA CA2692013A patent/CA2692013C/fr not_active Expired - Fee Related
- 2008-07-28 AU AU2008282903A patent/AU2008282903B2/en not_active Ceased
- 2008-07-28 MX MX2010001187A patent/MX2010001187A/es not_active Application Discontinuation
- 2008-07-28 KR KR1020107001995A patent/KR20100033418A/ko not_active Ceased
- 2008-07-28 EP EP08794832A patent/EP2220065A2/fr not_active Withdrawn
- 2008-07-28 SG SG2012056255A patent/SG183667A1/en unknown
- 2008-07-28 WO PCT/US2008/009142 patent/WO2009017719A2/fr not_active Ceased

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WO2009017719A3 (fr)	2009-04-23
MX2010001187A (es)	2010-03-04
SG183667A1 (en)	2012-09-27
CA2692013A1 (fr)	2009-02-05
AU2008282903A1 (en)	2009-02-05
KR20100033418A (ko)	2010-03-29
WO2009017719A2 (fr)	2009-02-05
WO2009017719A8 (fr)	2010-02-11
AU2008282903B2 (en)	2011-06-30
EP2220065A2 (fr)	2010-08-25

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2009-12-30	EEER	Examination request
2014-09-09	MKLA	Lapsed	Effective date: 20140729

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